KR20230171449A - 브루톤 티로신 키나제 억제제의 공결정질 형태 - Google Patents
브루톤 티로신 키나제 억제제의 공결정질 형태 Download PDFInfo
- Publication number
- KR20230171449A KR20230171449A KR1020237038658A KR20237038658A KR20230171449A KR 20230171449 A KR20230171449 A KR 20230171449A KR 1020237038658 A KR1020237038658 A KR 1020237038658A KR 20237038658 A KR20237038658 A KR 20237038658A KR 20230171449 A KR20230171449 A KR 20230171449A
- Authority
- KR
- South Korea
- Prior art keywords
- crystalline form
- lymphoma
- btk
- pharmaceutical composition
- weight
- Prior art date
Links
- 229940125814 BTK kinase inhibitor Drugs 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 41
- 206010028980 Neoplasm Diseases 0.000 claims description 54
- 201000011510 cancer Diseases 0.000 claims description 52
- 239000008194 pharmaceutical composition Substances 0.000 claims description 44
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 36
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 35
- 239000001361 adipic acid Substances 0.000 claims description 35
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 24
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 24
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims description 19
- 208000021937 marginal zone lymphoma Diseases 0.000 claims description 19
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 16
- 201000003444 follicular lymphoma Diseases 0.000 claims description 16
- 230000005855 radiation Effects 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 15
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims description 14
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims description 12
- 235000011037 adipic acid Nutrition 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 11
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 11
- 208000028564 B-cell non-Hodgkin lymphoma Diseases 0.000 claims description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 10
- 206010003246 arthritis Diseases 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- FWZAWAUZXYCBKZ-NSHDSACASA-N 5-amino-3-[4-[[(5-fluoro-2-methoxybenzoyl)amino]methyl]phenyl]-1-[(2S)-1,1,1-trifluoropropan-2-yl]pyrazole-4-carboxamide Chemical compound COc1ccc(F)cc1C(=O)NCc1ccc(cc1)-c1nn([C@@H](C)C(F)(F)F)c(N)c1C(N)=O FWZAWAUZXYCBKZ-NSHDSACASA-N 0.000 claims description 8
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 8
- 208000032568 B-cell prolymphocytic leukaemia Diseases 0.000 claims description 7
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
- 208000035416 Prolymphocytic B-Cell Leukemia Diseases 0.000 claims description 7
- 201000009277 hairy cell leukemia Diseases 0.000 claims description 7
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 6
- 208000011691 Burkitt lymphomas Diseases 0.000 claims description 6
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000036210 malignancy Effects 0.000 claims description 6
- ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 claims description 5
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 5
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 5
- 201000007924 marginal zone B-cell lymphoma Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims description 3
- 208000034578 Multiple myelomas Diseases 0.000 claims description 3
- 238000001228 spectrum Methods 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims 4
- 208000032843 Hemorrhage Diseases 0.000 claims 1
- FYUWIEKAVLOHSE-UHFFFAOYSA-N ethenyl acetate;1-ethenylpyrrolidin-2-one Chemical compound CC(=O)OC=C.C=CN1CCCC1=O FYUWIEKAVLOHSE-UHFFFAOYSA-N 0.000 claims 1
- 230000000527 lymphocytic effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 229940124291 BTK inhibitor Drugs 0.000 abstract description 3
- 238000012512 characterization method Methods 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 208000037765 diseases and disorders Diseases 0.000 abstract 1
- 102000001714 Agammaglobulinaemia Tyrosine Kinase Human genes 0.000 description 45
- 108010029445 Agammaglobulinaemia Tyrosine Kinase Proteins 0.000 description 45
- 229960000250 adipic acid Drugs 0.000 description 33
- 239000000203 mixture Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LSPHULWDVZXLIL-LDWIPMOCSA-N (?)-Camphoric acid Chemical compound CC1(C)[C@@H](C(O)=O)CC[C@@]1(C)C(O)=O LSPHULWDVZXLIL-LDWIPMOCSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- 238000010922 spray-dried dispersion Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 4
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 4
- 201000000050 myeloid neoplasm Diseases 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- GXIOLUHFFBICKA-MTQSPMMESA-N (1R,3S)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid Chemical compound CC1(C)[C@H](CC[C@@]1(C)C(O)=O)C(O)=O.CC1(C)[C@H](CC[C@@]1(C)C(O)=O)C(O)=O GXIOLUHFFBICKA-MTQSPMMESA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- -1 HPMCAS-L Chemical compound 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 208000017760 chronic graft versus host disease Diseases 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 3
- 230000003393 splenic effect Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- SRSYFANOKMRZEY-UHFFFAOYSA-N FC(C(C)N1N=CC(=C1)C(=O)N)(F)F Chemical compound FC(C(C)N1N=CC(=C1)C(=O)N)(F)F SRSYFANOKMRZEY-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002050 diffraction method Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- GXIOLUHFFBICKA-SXNOSCCBSA-N 1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid;(1r,3s)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O.CC1(C)[C@@H](C(O)=O)CC[C@@]1(C)C(O)=O GXIOLUHFFBICKA-SXNOSCCBSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241001085205 Prenanthella exigua Species 0.000 description 1
- 206010066901 Treatment failure Diseases 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000003070 absorption delaying agent Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000003519 mature b lymphocyte Anatomy 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000011476 stem cell transplantation Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002626 targeted therapy Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/14—Adipic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/06—Saturated compounds having a carboxyl group bound to a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Inorganic Chemistry (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163188747P | 2021-05-14 | 2021-05-14 | |
| US63/188,747 | 2021-05-14 | ||
| PCT/US2022/028663 WO2022240920A1 (fr) | 2021-05-14 | 2022-05-11 | Formes cocristallines d'un inhibiteur de la tyrosine kinase de bruton |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20230171449A true KR20230171449A (ko) | 2023-12-20 |
Family
ID=82019727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020237038658A KR20230171449A (ko) | 2021-05-14 | 2022-05-11 | 브루톤 티로신 키나제 억제제의 공결정질 형태 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP4337196A1 (fr) |
| JP (1) | JP2024517963A (fr) |
| KR (1) | KR20230171449A (fr) |
| CN (1) | CN117320712A (fr) |
| AU (1) | AU2022274771A1 (fr) |
| BR (1) | BR112023021235A2 (fr) |
| CA (1) | CA3217452A1 (fr) |
| IL (1) | IL308011A (fr) |
| WO (1) | WO2022240920A1 (fr) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013010136A2 (fr) | 2011-07-13 | 2013-01-17 | Pharmacyclics, Inc. | Inhibiteurs de tyrosine kinase de bruton |
| EP2548877A1 (fr) | 2011-07-19 | 2013-01-23 | MSD Oss B.V. | Dérivés de 4-(pyridine condensée à 5 chaînons)benzamide comme inhibiteurs de BTK |
| US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US9637486B2 (en) | 2013-12-20 | 2017-05-02 | Merck Sharp & Dohme Corp. | Btk inhibitors |
| JP6504548B2 (ja) | 2014-02-21 | 2019-04-24 | プリンシピア バイオファーマ インコーポレイテッド | Ｂｔｋ阻害剤の塩および固体形態 |
| CN114716381A (zh) | 2015-12-16 | 2022-07-08 | 洛克索肿瘤学股份有限公司 | 可用作激酶抑制剂的化合物 |
| KR20210034623A (ko) | 2018-07-20 | 2021-03-30 | 메르크 파텐트 게엠베하 | 다발성 경화증의 치료 및 예방을 위한 방법에서 사용하기 위한 치환된 아미노-피리미딘 화합물 |
| CA3224945A1 (fr) | 2018-07-31 | 2020-02-06 | Loxo Oncology, Inc. | Dispersions sechees par pulverisation, formulations et polymorphies de (s)-5-amino-3-(4-((5 fluoro-2-methoxybenzamido)methyl)phenyl)(1,1,1-trifluoropropan-2-yl)-1h-pyrazole-4-carboxamide |
| JP2023520469A (ja) | 2020-04-03 | 2023-05-17 | ジェネンテック， インコーポレイテッド | ブルトン型チロシンキナーゼの阻害剤を使用する再発性多発性硬化症の治療方法 |
-
2022
- 2022-05-11 EP EP22729864.3A patent/EP4337196A1/fr active Pending
- 2022-05-11 BR BR112023021235A patent/BR112023021235A2/pt unknown
- 2022-05-11 IL IL308011A patent/IL308011A/en unknown
- 2022-05-11 CN CN202280035134.XA patent/CN117320712A/zh active Pending
- 2022-05-11 JP JP2023570216A patent/JP2024517963A/ja active Pending
- 2022-05-11 CA CA3217452A patent/CA3217452A1/fr active Pending
- 2022-05-11 KR KR1020237038658A patent/KR20230171449A/ko active Search and Examination
- 2022-05-11 AU AU2022274771A patent/AU2022274771A1/en active Pending
- 2022-05-11 WO PCT/US2022/028663 patent/WO2022240920A1/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO2022240920A1 (fr) | 2022-11-17 |
| EP4337196A1 (fr) | 2024-03-20 |
| JP2024517963A (ja) | 2024-04-23 |
| AU2022274771A1 (en) | 2023-11-16 |
| IL308011A (en) | 2023-12-01 |
| CA3217452A1 (fr) | 2022-11-17 |
| CN117320712A (zh) | 2023-12-29 |
| BR112023021235A2 (pt) | 2023-12-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10428065B2 (en) | Isoxazolyl substituted imidazopyridines | |
| CN114423750B (zh) | 2,4-二取代嘧啶衍生物及其制备方法和用途 | |
| US10683274B2 (en) | 3-substituted carbonyl-naphtho[2,3-B]furane derivative or pharmaceutically acceptable salt thereof | |
| TW200813042A (en) | Six membered heteroaromatic inhibitors targeting resistant kinase mutations | |
| WO2018018986A1 (fr) | Composé de diphénylaminopyrimidine et de triazine, composition pharmaceutique et utilisation de celui-ci | |
| EP2964223A1 (fr) | Composés inhibant l'activité enzymatique de la kinase à motifs répétés riches en leucine | |
| EP3705478B1 (fr) | Composé triazine et son sel pharmaceutiquement acceptable | |
| WO2014137719A1 (fr) | Composés inhibant l'activité enzymatique de la kinase à séquence répétée riche en leucine | |
| EP4038063B1 (fr) | Composés hétérocycliques pour inhiber des activités de tyk2 | |
| CN113631557B (zh) | Jak激酶抑制剂及其制备方法和在医药领域的应用 | |
| CN114728170B (zh) | 对核受体具有活性的化合物 | |
| KR20190098266A (ko) | 치환된 축합 헤테로아릴기 화합물인 키나제 억제제 및 이의 응용 | |
| AU2004283093A1 (en) | Compounds and compositions as protein kinase inhibitors | |
| CA3153437A1 (en) | Selective dihydropyrrolopyrimidine jak2 inhibitors | |
| WO2023078451A1 (fr) | Composé utile en tant qu'inhibiteur de kinase cdk7 et son utilisation | |
| CN113549073B (zh) | 作为JAK抑制剂的吡唑并[1,5-a]嘧啶衍生物 | |
| WO2018133875A1 (fr) | Inhibiteur de kinase jak, son procédé de préparation et son utilisation | |
| KR20230171449A (ko) | 브루톤 티로신 키나제 억제제의 공결정질 형태 | |
| JP2023524863A (ja) | 三環式のヘテロ環 | |
| WO2017070135A1 (fr) | Promédicaments de dérivés 2-(4-(3-((4-amino-7-cyano-imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phényl)pipérazin-1-yl)propanamide utilisés comme inhibiteurs de ck2 pour le traitement du cancer | |
| CN112142731B (zh) | 一种2，4-二取代嘧啶衍生物及其制备方法和用途 | |
| CA3100095C (fr) | Compose d'indoline-1-formamide, son procede de preparation et son utilisation medicale | |
| WO2022112951A1 (fr) | Formes à l'état solide de sel de chlorhydrate de ((1s,2s,4r)-4-{4-[(1s)-2,3-dihydro-1h-inden-1-ylamino]-7h-pyrrolo[2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)méthyl sulfamate | |
| EP4303215A1 (fr) | Agoniste du récepteur glp-1, composition pharmaceutique le comprenant et son procédé de préparation | |
| WO2020233716A1 (fr) | Inhibiteurs de kinase imidazopyridazine mnk1/mnk2, procédé de préparation correspondant et utilisation associée |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination |